Dabco → HCID 131724317, compound

HRID 1840460Notes

Reaction equation

[Br:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:37])[C@@H:15]4[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]4[C:17]=3[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])[S:10][C:9]=12.[N:38]12[CH2:45][CH2:44][N:41]([CH2:42][CH2:43]1)[CH2:40][CH2:39]2>C(#N)C>[Br-:1].[N+:38]12([CH2:2][CH2:3][S:4][C:5]3[N:6]=[CH:7][N:8]4[CH:12]=[C:11]([C:13]5[C@H:14]([CH3:37])[C@@H:15]6[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]6[C:17]=5[C:18]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=5)=[O:19])[S:10][C:9]=34)[CH2:45][CH2:44][N:41]([CH2:42][CH2:43]1)[CH2:40][CH2:39]2

Participants

Conditions

Temperature: 50 °C

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[7-(2-bromoethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (177 mg) was dissolved in 5 ml of acetonitrile. 1,4-Diazabicylco[2,2,2]octane (43 mg) was added to the solution. The mixture was stirred at 50° C. for 12 hr. The reaction solution was concentrated, and the residue was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to prepare 184 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[2-(1-azonia-4-azabicyclo-[2,2,2]oct-1-yl)ethyl]thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide.

Workup

concentrationThe reaction solution was concentrated
customthe residue was purified by column chromatography on Sephadex
custom(chloroform:methanol=1:1) to prepare 184 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[2-(1-azonia-4-azabicyclo-[2,2,2]oct-1-yl)ethyl]thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide

Sources & evidence

ORD record: ord-2c5cf1586d1544afa2f61cc1987aa88b
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680313B2

Reaction notes

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